Mario Sundar

LinkedIn's 2nd PR hire. These are my thoughts on products, public relations, and startups.

Hacking Time and To dos

To dos, like New Year’s resolutions, are a Herculean challenge that most of us have tried and failed. Nothing works. Paul Ford), former editor Harper’s Magazine, thinks we repeatedly waste time building to-do applications with no serious solution in sight:

One of the systems Victor talks about is in that speech is Doug Engelbart’s NLS system of 1968, which pioneered a ton of things—collaborative software, hypertext, the mouse—but deep, deep down was a to-do list manager. Since then the world of technology has never hurt for personal productivity tools.

Every year or two there seems to be a new hotness: it was Remember the Milk for a while, and OmniFocus, and TaskPaper, and Asana. Asana’s tagline is “Teamwork without email.” And of course there are tons of productivity technologies that don’t involve a computer, including the “Getting Things Done” system, which tore through the Internet like wildfire for a few years—Inbox Zero is its legacy.

That said, I believe we are at the cusp of upcoming technologies like speech recognition, the evolution of notifications, and a renewed focus on what I’d like to call “life management” (think wearables) that will finally put a dent in the way we manage our lives, to dos included. A couple of examples that have attacked this problem with some level of success have been “Mailbox” and “Google Now” to cite a couple of examples. Sure, these are early attempts at fixing email and to-dos, but I see this as a harbinger of the future.

The Challenge with To-dos

The biggest challenge with time management apps is the fluid requirements of To do apps. They have to scale from the micro (staying focused on the immediate task at hand) to the macro (that needs perspective with other apps like the calendar, ideally with notifications); the simple to the complex, the one-time to the repetitive (like habit tracker @liftapp); the important & urgent to the trivial; and so far we’ve just had blunt instruments with which we’ve been trying to hack away at this complexity called life.

All this complexity also has to be handled with little input from the user, or you risk losing them at the get-go should you try to gather much information from them. And the input medium has to be as simple as possible, not forcing the user to be typing away with difficulty on their smartphones. That’s where Google Now becomes more and more magical, as they delight their users by surfacing information users might have missed. This will be the future of To-dos. Read through Search Engine Land, Danny Sullivan’s post comparing predictive search to digital assistants:

However, there’s no question that Google Now has proven that there are some search needs that can be predicted. These are often especially tied to location. That’s why — in retrospect — it’s not surprising that predictive search has emerged as more a smartphone feature rather than a search engine feature. We got Google Now for our phones long before we got it for our desktops.

Indeed, predictive search may even develop into an essential smartphone feature. We may come to expect every phone to have it, just as we expect our phones to have cameras or notification areas. And just as people might not buy a phone deemed to have a bad camera, they might also pass over a phone with poor predictive search in favor of one offering better.

The other major challenge with to-dos is handing off some of their actions to apps like email and calendar. Like some to-dos, that are important or urgent, could very well be a unit on your calendar. Now how does one hand that off across apps?

[Update: Since the writing of the post, Khosla VenturesTimeful App launched on iOS this past week, and seems to do a terrific job thus far. More on that in an upcoming post]

Now if only there was a way to dumb down this process to its fundamental basics, where the user does none of the heavy lifting but experiences the benefits of (feedback loop) of such a system, we might have a start. Granted we do not have a single solution that is cross-application and cross-platform, yet.

Hacking To-dos with Siri

This past weekend, upon transitioning to Apple’s latest OS X Yosemite, I feel I may have a quick fix, at least for now that might ease my time management. [This post was written before the launch of Timeful, so expect a sequel shortly.] Two of the biggest improvements in Yosemite, besides the mobile iOS influenced look-and-feel are Notifications (at a swipe) and Reminders that (finally!) syncs across mobile and desktop.

And the secret sauce to make this time management hack work is Siri. In its most recent avatar, Siri is a pretty good note taker, transcriber, and so removes the biggest obstacle with Reminders, which is the act of opening an app to type in your to-do, now all you’ve to do is say it out loud and it’s integrated into a giant catch-all. Let’s call that folder: “Do.”

In addition, I’ve created a bunch of often repeated categories, which range from Groceries (which I turn to when I shop at Google Shopping Express or Instacart), to Chores, which I’d rather not turn to, but gotta. At the end of each day, I review the “Do” folder and either assign a time / date for completion, either / or a folder that I can turn to “Later.”

The missing piece to all To-dos is Timing. Notifications (across mobile and desktop) can really make this work, unlike all past attempts at To-do apps. The good news with the new Mac OS’s is that Notifications are integrated cross-platform and a cursory viewing is just a swipe away under the newly redesigned OS X on the right hand of the desktop.

Frankly, this is as good as Reminders are gonna get for now, but I bet there are ways to further do the thinking for us, as Google Now has shown.

The Future is Brighter

With my experience with Timeful these past 24 hours, it’s clear that time management can be hacked on mobile and desktop in a way we haven’t been able to do thus far. And with increasing tie-ins with the mobile OS and the world of notifications (check out Naveen‘s (Partner, Expa) essay on how “notifications are becoming the app itself”) and predictive search, we just might be able to crack this case.

Also, notifications will allow time management apps to interact with the user on a project to project basis in a way that task managers haven’t been able to in the past. The benefits of such one-click incremental interactions (task done or task moved forward) in future OS’s will bring about a sea change in the efficiency of to-do apps.

When we can interact with our data in short bursts via notifications, we make remarkable efficiency gains, especially on tasks that we perform again and again. Apps will become more about information and communications; we’re going to think of them as services instead of as windows onto our data. The things that can make best use of single click efficiency will soar. A whole new world is up there waiting for us at the top of the screen. We just need to pull it down.

Finally, one of the time management fads talked about in Paul Ford’s piece was David Allen and his until recently ubiquitous Getting Things Done (GTD) craze in the nerd community. Even comedian Drew Carey outsourced his time management to Allen to fix this problem and learned this:

[It] turns out that the Zeigarnik effect is not, as was assumed for decades, a reminder that continues unabated until the task gets done. The persistence of distracting thoughts is not an indication that the unconscious is working to finish the task. Nor is it the unconscious nagging the conscious mind to finish the task right away. Instead, the unconscious is asking the conscious mind to make a plan.

And that plan needs to be made in concert with the big picture, without which the minute next steps mean nothing. Curious what David Allen thinks of the new wave of time management?

How do you track time in your life? Curious if any of your time hacks beat the version I outline above. Tweet me @mariosundar or just leave a comment below.

Filed under: HOW-TO Use Social Media, New Products, What's New in Social Media

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